NPASS Compound

Natural Product: NPC20050

Natural Product ID	NPC20050
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Beta,3Beta-Epoxy-5,7,3',4'-Tetrahydroxyflavan-(4Alpha->8)-Epicatechin
IUPAC Name	(2R,3R)-8-[(1aR,7S,7aS)-1a-(3,4-dihydroxyphenyl)-4,6-dihydroxy-7,7a-dihydrooxireno[2,3-b]chromen-7-yl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3120540
PubChem CID	76325280
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 66 72 0 0 0 0 0 0 0 0999 V2000 -2.7964 2.5489 -0.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7935 3.7793 0.5891 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4419 3.8391 1.9272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0989 2.6786 2.5900 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1105 1.4571 1.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 1.3841 0.5802 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 0.0965 -0.1426 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7509 -0.6695 0.0899 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5242 -1.9269 0.8919 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4005 -2.7349 0.3605 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4650 -4.1089 0.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3769 -4.7874 -0.2514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2402 -4.1207 -0.6419 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1900 -2.7387 -0.5266 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0256 -2.0509 -0.9306 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0101 -1.8650 0.1611 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7836 -2.3490 1.4356 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7673 -2.1363 2.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9351 -1.4722 2.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1214 -1.0055 0.8083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1677 -1.1929 -0.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 -0.7413 -1.4936 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1202 -0.1207 -2.0533 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2008 1.3648 -2.0410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1605 2.1855 -1.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3006 3.5650 -1.7034 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4873 4.1712 -2.0620 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5442 3.3660 -2.4145 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3804 2.0000 -2.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7375 3.9706 -2.7752 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6165 5.5698 -2.0682 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8837 -0.7871 -1.6928 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4171 -0.7598 -3.0327 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8885 -1.2797 3.0540 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6007 -3.0261 1.7436 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2567 -2.0475 -0.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3159 -0.6783 0.1297 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8636 -4.8331 -1.1543 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5917 -4.7934 0.6359 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5979 0.1523 0.8335 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7509 2.7680 3.9303 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4384 5.0699 2.5888 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0725 2.4965 -1.1239 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0630 4.7013 0.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8454 0.5542 2.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4309 0.2974 -1.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2904 -0.9087 -0.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4424 -2.5452 0.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3993 -1.6480 1.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3742 -5.8782 -0.3594 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5698 -2.7670 -1.6420 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5851 -2.5180 3.3803 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0411 -0.4716 0.5347 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2188 1.7914 -1.4058 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4680 4.2263 -1.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2255 1.3917 -2.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5760 3.9672 -2.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9357 6.0672 -1.2619 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0509 -0.1863 -1.6872 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6458 -1.3993 4.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2154 -3.0315 2.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1047 -5.6816 -0.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5696 -5.6961 1.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3524 0.1761 1.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2250 3.4265 4.5542 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7153 5.8951 2.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 6 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 23 32 1 0 32 33 1 0 19 34 1 0 17 35 1 0 14 36 2 0 36 37 1 0 13 38 1 0 11 39 1 0 8 40 1 0 4 41 1 0 3 42 1 0 6 1 1 0 37 7 1 0 36 10 1 0 32 15 1 0 21 16 1 0 33 23 1 0 29 24 1 0 1 43 1 0 2 44 1 0 5 45 1 0 7 46 1 6 8 47 1 6 9 48 1 0 9 49 1 0 12 50 1 0 15 51 1 6 18 52 1 0 20 53 1 0 25 54 1 0 26 55 1 0 29 56 1 0 30 57 1 0 31 58 1 0 32 59 1 6 34 60 1 0 35 61 1 0 38 62 1 0 39 63 1 0 40 64 1 0 41 65 1 0 42 66 1 0 M END

Standard InCHIKey	MSVVDBMAVSBGAQ-OUECKCITSA-N
Standard InCHI	InChI=1S/C30H24O12/c31-13-7-20(37)24-23(8-13)41-30(12-2-4-16(33)19(36)6-12)29(42-30)26(24)25-21(38)10-17(34)14-9-22(39)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-27,29,31-39H,9H2/t22-,26+,27-,29+,30+/m1/s1
SMILES	c1cc(c(cc1[C@@H]1[C@@H](Cc2c(cc(c([C@@H]3c4c(cc(cc4O[C@]4(c5ccc(c(c5)O)O)[C@H]3O4)O)O)c2O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.13	Volume:	541.386 ? Van der Waals volume.
Dense:	1.064	LogP:	1.771 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.969 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.951 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	213.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.127	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.75	Fsp³:	0.2
MCE-18:	143.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.895	Fluc inhibitor:	0.289 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.64 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.73 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.488	Promiscuous compounds:	0.163

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.967	MDCK Permeability:	-4.805
Pgp-inhibitor:	0.0	Pgp-substrate:	0.156
PAMPA:	0.159 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.968
Plasma Protein Binding (PPB):	90.331%	Volume Distribution (VD):	0.04
Fu:	15.376% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.105
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.996	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.164	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.492
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.336

Half-life (T1/2):

3.908

ADMET: Toxicity

hERG Blockers:	0.128	hERG Blockers (10um):	0.881
Human Hepatotoxicity (H-HT):	0.85	Drug-induced Liver Injury (DILI):	0.822
AMES Toxicity:	0.631	Rat Oral Acute Toxicity:	0.819
Maximum Recommended Daily Dose:	0.988	Skin Sensitization:	1.0
Carcinogencity:	0.028	Eye Corrosion:	0.0
Eye Irritation:	0.815	Respiratory Toxicity:	0.918
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.954
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.104
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.972
BCF:	1.411 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.861 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.311 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.548 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	4
Activity	6

Activity Type	# Activity
Individual protein	4
Non-molecular	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4416	Individual protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	106.67	%	PMID[19942326]
NPT4416	Individual protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	216.77	%	PMID[25495797]
NPT4416	Individual protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	97.95	%	PMID[21130542]
NPT4416	Individual protein	Tartrate-resistant acid phosphatase type 5	Mus musculus	Inhibition	=	199.06	%	PMID[19124662]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	109.85	%	PMID[24485782]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	185.08	%	PMID[24485782]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	103.38	%	PMID[24485782]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	240.74	%	PMID[24485782]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	34.72	uM	PMID[24485782]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	5.22	uM	PMID[24485782]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC20050 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	24453
0.1-0.2	23123
0.2-0.3	2033
0.3-0.4	125
0.4-0.5	48
0.5-0.6	43
0.6-0.7	31
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC306267
0.6667	Remote Similarity	NPC58190
0.6667	Remote Similarity	NPC108811
0.6667	Remote Similarity	NPC170103
0.6667	Remote Similarity	NPC236202
0.6667	Remote Similarity	NPC262911
0.6667	Remote Similarity	NPC202742
0.6575	Remote Similarity	NPC246202
0.6575	Remote Similarity	NPC224161
0.6575	Remote Similarity	NPC46335
0.6575	Remote Similarity	NPC279406
0.6575	Remote Similarity	NPC486519
0.65	Remote Similarity	NPC135021
0.6494	Remote Similarity	NPC272552
0.6494	Remote Similarity	NPC226108
0.6494	Remote Similarity	NPC322899
0.6463	Remote Similarity	NPC147743
0.6463	Remote Similarity	NPC4809
0.6463	Remote Similarity	NPC73517
0.641	Remote Similarity	NPC302549
0.6235	Remote Similarity	NPC106601
0.6235	Remote Similarity	NPC151474
0.6203	Remote Similarity	NPC46283
0.6203	Remote Similarity	NPC469944
0.6203	Remote Similarity	NPC278548
0.6173	Remote Similarity	NPC478616
0.6173	Remote Similarity	NPC478339
0.6163	Remote Similarity	NPC212614
0.6163	Remote Similarity	NPC205613
0.6125	Remote Similarity	NPC44192
0.6118	Remote Similarity	NPC86630
0.6	Remote Similarity	NPC134911
0.5974	Remote Similarity	NPC313116
0.5974	Remote Similarity	NPC603340
0.5955	Remote Similarity	NPC159526
0.5934	Remote Similarity	NPC185231
0.5862	Remote Similarity	NPC78074
0.5823	Remote Similarity	NPC70409
0.5823	Remote Similarity	NPC204770
0.5823	Remote Similarity	NPC600551
0.5823	Remote Similarity	NPC601980
0.5823	Remote Similarity	NPC602065
0.5823	Remote Similarity	NPC611024
0.5735	Remote Similarity	NPC261619
0.5735	Remote Similarity	NPC61477
0.5735	Remote Similarity	NPC78770
0.5735	Remote Similarity	NPC219876
0.5735	Remote Similarity	NPC126029
0.5735	Remote Similarity	NPC15658
0.5679	Remote Similarity	NPC600630
0.5679	Remote Similarity	NPC607896
0.5679	Remote Similarity	NPC611369
0.5647	Remote Similarity	NPC471404
0.5641	Remote Similarity	NPC184245
0.5641	Remote Similarity	NPC187801
0.5641	Remote Similarity	NPC610920
0.5618	Remote Similarity	NPC478337
0.5618	Remote Similarity	NPC478338
0.5584	Remote Similarity	NPC277331
0.5584	Remote Similarity	NPC100482
0.5556	Remote Similarity	NPC226809
0.5526	Remote Similarity	NPC96576
0.5513	Remote Similarity	NPC294558
0.5513	Remote Similarity	NPC18185
0.5513	Remote Similarity	NPC263940
0.5506	Remote Similarity	NPC478340
0.55	Remote Similarity	NPC155564
0.5484	Remote Similarity	NPC478617
0.5366	Remote Similarity	NPC211561
0.519	Remote Similarity	NPC601999
0.5181	Remote Similarity	NPC601997
0.5181	Remote Similarity	NPC609211
0.5181	Remote Similarity	NPC610665
0.5135	Remote Similarity	NPC178054
0.5062	Remote Similarity	NPC165483

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC20050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5405
0.1-0.2	3717
0.2-0.3	20
0.3-0.4	6
0.4-0.5	0
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5735	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD1613	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data